Caught and blackmailed

Everyone in this story is 18+

## Act I: The Discovery

Kevin was eighteen years old and, by all reasonable metrics, a perfectly normal boy. He played video games. He was mediocre at soccer. He had exactly one crush, a girl named Madison who sat two rows ahead of him in Chemistry and who had, on one glorious occasion, said "nice hoodie" to him, a sentence he had replayed in his head approximately four thousand times.

What nobody knew — not his friends, not his parents, and certainly not Madison — was that Kevin had a secret. A silky, lacy, slightly-too-small secret.

It had started innocently enough. Kevin, being the kind of bored teenager who investigates things, had wandered into his older sister Chloe's room one afternoon while she was out. Chloe was nineteen and away at college most of the year, which meant her room was a veritable museum of interesting things. He'd been looking for a charger. He had found so much more.

Her lingerie drawer was open. And there, draped across the top like a silken promise, was a matching black lace set — bra, panties, and a garter belt with actual stockings. Kevin stared at it. The panties were tiny. The bra was... complicated. He touched the fabric. It was soft. Softe than any underwear he'd ever owned, and his underwear was a rotating cast of grey boxer-briefs that had been washed so many times they'd achieved a kind of philosophical neutrality.

He put them on.

He doesn't know why. He just did. He stripped down and pulled on the panties and they hugged his hips in a way that felt frankly illegal, and he hooked the bra behind his back on the fourth try, and then he put on the stockings and the garter belt because they were *right there* and he was already this deep.

He looked in Chloe's mirror.

And Kevin had what can only be described as a *moment*.

He looked *good*. Like, weirdly, genuinely, inexplicably good. The black lace against his pale skin, the way the stockings made his legs look longer, the way the bra — even empty — gave his shoulders a certain elegance. He looked like a boy who had accidentally stumbled into the Victoria's Secret catalog and decided to stay.

He was hooked.

## Act II: The Collection

Over the next few months, Kevin became a lingerie connoisseur, which is a ridiculous sentence to write about a eighteen-year-old boy but there it is. He bought his own sets. Cheap ones from Amazon, because he was a teenager and not a Saudi prince. A red lace bodysuit. A white satin set with a little bow on the panties that made him feel like a birthday present. A sheer black teddy that was frankly a bit much for a Tuesday but Kevin had *range*.

And every time, he took photos.

This was the important part. The *system*. Kevin would dress up, take photos from every angle, study them like a scientist, and then delete them from his camera roll so nobody would ever see them. Because if someone saw them, they would *know*, and if they knew, they would *judge*, and Kevin was not emotionally prepared for judgment.

The problem — the fatal flaw, the crack in the foundation of his entire operation — was that Kevin did not use a secure photo app. He did not use a hidden folder. He did not do the one thing that any reasonable person would do.

Kevin took the photos and then just... left them in his camera roll. Right there in the open. Mixed in with selfies of his face and photos of his dog and blurry shots of homework. The lingerie photos sat in the same gallery as everything else, one scroll away from total exposure, like a bomb waiting to go off.

It was only a matter of time.

## Act III: The Drunk Text

The night of the incident, Kevin was at a party. A party with alcohol. Kevin, being eighteen, had consumed approximately three beers and was feeling the specific brand of invincible-stupid that only a teenager with a blood alcohol content of "probably fine" can achieve.

He was sitting on a couch, scrolling his phone, when Madison walked by. Madison! His crush! She was at the party! She waved at him! His brain short-circuited and he waved back with a delay that was probably noticeable but let's not dwell on it.

And then, later, alone in a corner, buzzed and bold, Kevin had an idea. *The* idea.

He would send Madison a photo. A normal one. A selfie. Something casual. *Hey, weird seeing you at this party, haha.* Chill. Normal. No lingerie. Just his face.

He opened his camera roll and scrolled.

And scrolled.

And his thumb, in its infinite drunken wisdom, landed on a photo. He looked at it for half a second. It was him. It was a photo of him. He sent it.

He sent it and put his phone away and went back to the party.

The photo he sent was not a selfie.

The photo he sent was Kevin in the red lace bodysuit, full body, in front of his bathroom mirror, holding his phone at chest height, his face partially obscured because he'd taken it at a bad angle, one hand on his hip, looking like a Victoria's Secret model who had somehow wandered into the body of a teenage boy.

He had sent Madison the red lace bodysuit photo.

And he had not noticed.

## Act IV: The Aftermath

Madison looked at her phone.

She had gotten a message from Kevin, the boy from Chemistry who had once said "you too" when the teacher said "have a good weekend" to him, and she had opened it expecting a "hey."

She got a "hey" all right. She got a "hey" in *red lace*.

Madison looked at the photo. She zoomed in. She zoomed out. She looked at it again.

She laughed. She laughed so hard she had to put her phone down. She laughed so hard her friend asked what was so funny and she showed her and her friend laughed too. She screenshotted the photo — for posterity, for the archive, for the eventual trial — and then she did the thing that would seal Kevin's fate forever.

She sent it to Chloe.

*"Is this your brother????"*

Chloe, who had been wondering for months why her lingerie drawer was never quite where she left it, looked at the photo and felt a profound sense of vindication.

*"OH MY GOD"* she replied. *"THAT'S MY BODysuit"*

*"HE'S WEARING YOUR LINGERIE??"*

*"THAT'S THE RED ONE. HE TOOK MY RED ONE."*

And then, because they were both nineteen-ish and evil in the way that older sisters and their friends are evil, they made a plan.

## Interlude: The Plan

The plan was simple. Their parents were going away for a week — a whole week — to visit their aunt in another state. Chloe would be home from college for fall break. Madison, who lived two streets over and was basically family at this point, would be staying over "to keep Chloe company."

Kevin would be there too.

Kevin, who did not know that Madison had seen the photo. Kevin, who did not know that Madison had told Chloe. Kevin, who did not know that the two of them had spent an entire group call cackling and planning and saying things like "we're going to have *so* much fun" in a tone that should have warned him.

Kevin thought he was going to have a normal week at home with his sister.

Kevin was wrong.

## Act V: The Week

**Day 1 — The Ambush**

Kevin walked in the door after school to find Chloe and Madison sitting on the couch, waiting for him. They had the photo pulled up on Chloe's laptop. They had it *maximized*.

"So," Chloe said, "anything you want to tell us?"

Kevin looked at the screen. He looked at his sister. He looked at his crush. His crush, who was smiling at him in a way that could only be described as predatory.

"...That's not me," Kevin said.

"That's literally your bathroom," Chloe said.

"It's a different bathroom."

"It's the same shower curtain."

Kevin crumbled.

Over the next hour, Kevin was interrogated. He confessed to everything. The lingerie drawer. The Amazon purchases. The secret photo shoots. The *collection*. He confessed and he was mocked and he was teased and at some point Madison said "you have better taste than Chloe" and Chloe said "excuse me?" and there was a brief sidebar argument, and Kevin, for one shining moment, felt like maybe he was going to get out of this with his dignity intact.

Then Chloe said, "so we've been talking, and we think you should wear it for us. For the week."

Kevin's heart stopped.

"For the *week*?"

"For the week."

**Day 2 — The Makeover**

The next day, Kevin came home to find the living room turned into a salon. Chloe had brought out her entire makeup kit. Madison had brought her own. There was a chair in the middle of the room and the chair was for Kevin.

"Sit," Madison said.

Kevin sat.

What followed was two hours of feminization that Kevin was not prepared for. Chloe did his foundation — *"you have good skin, actually, this is annoying"* — and Madison did his eyes and between them they did his lips and his blush and